Potassium Hydroxide → HCID 68294316, compound

HRID 1850070Notes

Reaction equation

HRID 1850070 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:16][C:15](=[CH:17][C:18]4[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][C:19]=4[Cl:28])[CH2:14]3)[CH:10]=2)[CH:5]=[CH:4]1>CO>[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][N:13]3[CH2:14][C:15](=[CH:17][C:18]4[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=4[Cl:28])[CH2:16]3)[CH:10]=2)[CH:5]=[CH:4]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68294609HCID 68294609, compound

Product 1

HCID 68294316HCID 68294316, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 M aqueous solution of KOH (1.5 mL) was added to a solution of methyl 4-((1-((1H-indol-6-yl)methyl)azetidin-3-ylidene)methyl)-3-chlorobenzoate (0.3 g, 0.82 mmol) in MeOH (7 mL) and the mixture was stirred at room temperature overnight. The mixture was then evaporated under reduced pressure and water (10 mL) was added to the residue. The solution was carefully acidified to pH 5 with a 3 M aqueous solution of HCl. The precipitated solid was extracted with ethyl acetate. The EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL). It was dried (Na2SO4), filtered, and concentrated in vacuo to give 4-((1-((1H-indol-6-yl)methyl)azetidin-3-ylidene)methyl)-3-chlorobenzoic acid as a white solid (0.26 g). ES+(M+H)+353.

Workup

  1. customThe mixture was then evaporated under reduced pressure and water (10 mL)
  2. additionwas added to the residue
  3. extractionThe precipitated solid was extracted with ethyl acetate
  4. washThe EtOAc layer was washed with water (2×10 mL) and brine (1×15 mL)
  5. dry with materialIt was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ae7bb0ea192f415f8ceb7a218df25c45
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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